Formation of β-carbolines from 1-[(1′ -carboxy-2′-indol-3′-yl-ethyl)amino]-1-deoxy-D-fructose under electron impact conditions
✍ Scribed by Varoujan Yaylayan; J. R. Jocelyn Paré; Richard Laing; Peter Sporns
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 339 KB
- Volume
- 25
- Category
- Article
- ISSN
- 1076-5174
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✦ Synopsis
Abstract
Interest in β‐carbolines has recently increased owing to their detection in human tissue and in some food products; one of the possible sources of their formation in food is the Amadori rearrangement product (ARP) of tryptophan with glucose, l‐[(1′‐carboxy‐2′‐indol‐3′‐ylethyl)amino] ‐1‐deoxy‐D‐fructose. Based on the intermediates identified in the high‐resolution electron impact spectrum of the tryptophan Amadori product and by B/E and B^2^/E linked‐scan experiments, a mechanism is proposed for their formation under electron impact conditions. The proposed mechanism is an intramolecular nucleophilic substitution reaction of the dehydrated tryptophan ARP, leading to the formation of 3‐substituted β‐carbolines; this mechanism might shed some light on the origin of their abundant formation in food.